CN106928386B - Preparation method of alkylstyrene polymer - Google Patents
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Abstract
The invention provides a preparation method of an alkylstyrene polymer, which comprises the steps of replacing nitrogen for three times in a glove box under normal pressure, adding ionic liquid serving as a solvent into a reactor in a low-temperature bath tank at the temperature of-10 to-100 ℃, adding alkylstyrene, and shaking for 10-20 min; and adding an initiator, stirring for reacting for 1-4 hours, adding a terminator to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain a sample. The properties of the polymer are as follows: the polymerization conversion rate is more than or equal to 82 percent, the molecular weight of the polymer is 1.5-2.5 ten thousand, the molecular weight distribution is 1.7-1.9, and the thermal decomposition temperature of the polymer is more than or equal to 300 ℃.
Description
Technical Field
The invention relates to a method for preparing an alkyl styrene polymer, in particular to a method for preparing an alkyl styrene polymer by using a solution method.
Background
The ionic liquid is an ionic compound which is completely composed of negative ions and positive ions and is liquid at normal temperature. Since Wilkes et al succeeded in synthesizing the first water and air stable 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid [ Emim ] [ BF4], the application of ionic liquids has been rapidly developed. Compared with the traditional solvent, the ionic liquid has a plurality of excellent characteristics: the steam pressure is low, the non-volatile, non-combustible and non-explosive; the melting point is low, the temperature range of the liquid state is wide, and the thermal stability and the chemical stability are good; can be recycled and regenerated, has no environmental pollution, and becomes a world-recognized clean green solvent for chemical production.
CN201410078284.6 relates to a preparation method of poly (isobutylene-co-p-methylstyrene) random copolymer, which adopts piperidine as a third component and alkyl aluminum as an initiator to successfully synthesize the poly (isobutylene-co-p-methylstyrene) random copolymer through positive ion copolymerization; has better molecular weight and molecular weight distribution. A method for synthesizing a poly (isobutylene-co-p-methylstyrene) random copolymer is provided, which is suitable for preparing the poly (isobutylene-co-p-methylstyrene) random copolymer by a slurry method and a solution method. CN 201010514252.8A method for preparing isoolefin copolymer; in halogenated hydrocarbon, hydrocarbon compound or their mixture, under the action of catalyst, making isoolefine monomer, multiolefine monomer and optional other copolymerizable monomer undergo the polymerization reaction, the described catalyst is the mixture of ethyl aluminium sesquichloride and water; the method for synthesizing the isoolefin copolymer by the environment-friendly and efficient solution method can solve the problem of low yield of the butyl rubber product by the solution method, simultaneously prolongs the continuous polymerization time of the reaction kettle, reduces the cleaning times, carries out polymerization at the relatively economic polymerization temperature of (-20 to-80 ℃), and is beneficial to energy conservation; saturated alkane is adopted as a solvent to replace methyl chloride used in a slurry method, which is beneficial to environmental protection. The preparation method of the CN201310546657.3 butyl rubber comprises the following steps: the raw material is prepared from isobutene and isoprene; polymerization: adding the raw materials into a polymerization kettle, then sequentially adding the catalyst and the diluent, and finally carrying out polymerization reaction for 2-4 hours at the temperature of-10 to-25 ℃ and under the condition of 1-14 KPa; and (4) terminating: adding isopropanol as a terminator after polymerization reaction, carrying out flash evaporation on the obtained polymer to remove unreacted monomers and solvents, and carrying out dehydration, extrusion, drying and briquetting to obtain a finished product of the butyl rubber. CN201310056027.8 a process for preparing a halogenated butyl elastomer graft copolymer, comprising: mixing a solution of a halobutyl elastomer with a phase transfer catalyst in the presence of a solution of an alkali metal salt of an oxygen or sulfur nucleophile bound to the polymer matrix, and grafting the polymer matrix to the halobutyl elastomer by nucleophilic substitution of allyl halide sites, wherein the halobutyl elastomer comprises repeating units derived from at least one C4 to C7 isoolefin monomer and at least one C4 to C14 multiolefin monomer, the halobutyl elastomer having allyl halide sites. CN 201210332453.5A process for preparing a butyl rubber solution, comprising the following steps: dehydrating the butyl rubber micelle water mixture through a vibrating screen; dissolving the dehydrated colloidal particle water mixture obtained above in alkane and/or cycloalkane as solvent to obtain aqueous colloidal solution; performing primary dehydration on the obtained aqueous glue solution through gravity settling dehydration to obtain aqueous glue solution; and carrying out secondary dehydration on the aqueous glue solution obtained in the previous step through electric dehydration to obtain a butyl rubber solution with the water content of less than 0.3 weight percent based on the total weight of the butyl rubber solution.
CN201310521634.7 discloses a method for preparing collagen microfiber based on imidazole type ionic liquid/dimethyl sulfoxide system. The method comprises the steps of taking animal leather as a raw material, taking an imidazole type ionic liquid/dimethyl sulfoxide mixture as a treating agent, treating at 90-130 ℃ to obtain a suspension, centrifuging at a high speed to obtain a precipitate, cleaning the obtained precipitate, and freeze-drying to obtain the collagen microfiber. CN201210196327.1 a process for the preparation of 2- (((1H-benzo [ d ] imidazol-2-yl) methyl) (1-benzyl-1H-benzo [ d ] imidazol-2-yl) amino) acetic acid, more specifically, 2- (((1H-benzo [ d ] imidazol-2-yl) methyl) (1-benzyl-1H-benzo [ d ] imidazol-2-yl) amino) acetic acid and intermediate compounds involved in the synthesis. The method for preparing the novel bisbenzimidazole amino acid compound 2- (((1H-benzo [ d ] imidazole-2-yl) methyl) (1-benzyl-1H-benzo [ d ] imidazole-2-yl) amino) acetic acid (VII) with potential bioactivity provides a thought for synthesis of similar compounds, and also provides a raw material for subsequent pharmacological research of the similar compounds. CN201310533308.8 chiral pyrrolidine functionalized imidazole salt, and a preparation method and application thereof. The chiral pyrrolidine functionalized imidazole salt is brominated 1- [2- (S) - (pyrrolidinyl) methyl ] -3-phenacyl imidazole hydrobromide. The preparation method comprises the following steps: taking natural amino acid L-proline as a starting material, and carrying out multiple steps of conventional organic synthesis reactions such as Boc acylation, carboxylic acid reduction, hydroxyl sulfonylation, nucleophilic substitution of imidazole negative ions, quaternary ammonium salinization of halogenated hydrocarbon, Boc protection removal and the like to prepare the chiral pyrrolidine functionalized imidazole salt. CN201310253407.0 emulsion resin for high throwing power cathode electrophoretic paint and a preparation method thereof, the emulsion resin is composed of three components: the modified epoxy resin accounts for 50-70% of the solid weight of the emulsion resin; the isocyanate at the closed end accounts for 20-40% of the solid weight of the emulsion resin; and (2) adding the modified epoxy resin, the closed-end isocyanate, the imidazolium salt compound and the solvent in sequence, heating to 60 ℃, uniformly stirring, keeping the temperature for 30 minutes, adding the organic acid for neutralization, stirring for 1 hour at 60 ℃, slowly adding deionized water under the stirring state, and continuously stirring for 30 minutes after the addition to obtain the resin emulsion, wherein the imidazolium salt compound accounts for 10-20% of the solid weight of the emulsion resin.
EP2285851(B1), JP5409774(B2) relate to block copolymers and polymer units having the formula A-B formed from a polymer of α from olefin units of 6 to 22 carbon atoms, B being substantially formed from isobutylene units, to a process for their preparation, to lubricating oil compositions for use therewith and to lubricant compositions comprising such block copolymers JP2000319461(A) gives resin composition products having excellent impact resistance which comprise a transparent polypropylene resin and an isobutylene polymer, a copolymer containing ethylene and α -olefin KR20010049193(A) provides a vinyl-containing polymer and a process for its preparation which can be used as an alternative to α polyisobutylene and poly-olefin and can be used in the production of lubricating oils.
Disclosure of Invention
The invention aims to provide a preparation method of an alkylstyrene polymer, and the prepared polymer has higher heat resistance.
The preparation method of the alkylstyrene polymer comprises the following steps: under normal pressure, replacing nitrogen in a glove box for three times, adding ionic liquid serving as a solvent into a reactor in a low-temperature bath tank at the temperature of-10 to-100 ℃, adding alkyl styrene, and uniformly stirring; adding an initiator, continuously stirring for reacting for 1-4 hours, adding a terminator to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer.
The temperature of the low-temperature bath in the glove box is-20 to-50 ℃.
The alkylstyrene can be one of o-methylstyrene, m-methylstyrene, p-methylstyrene, o-ethylstyrene, m-ethylstyrene, p-ethylstyrene, o-propylstyrene, m-propylstyrene, p-propylstyrene or styrene with a side chain of C4-C10, preferably o-methylstyrene; the dosage is 10-20 g.
The ionic liquid is imidazole salt, such as one or a mixture of 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt, 1-octyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt and 1-hexyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt, and the using amount of the ionic liquid is 2-5 g.
The terminator is methanol, and the dosage of the terminator is 0.5-2 g.
The initiator is ethyl sesquialuminum chloride, and can be one of ethyl aluminum dichloride and triethyl aluminum trichloride, and the using amount of the initiator is 0.2-1 g.
The initiator of the invention can be prepared according to the following method: preparing an initiator in the other bottle with the opening in the glove box low-temperature bath tank, adding 0.2-1 g of ethyl aluminum sesquichloride by using an injector, diluting with 1-5 ml of hexane, shaking up and standing for 5-20 min.
The polymer obtained by the invention has the following properties: the conversion rate of the polymer is more than or equal to 82 percent, the molecular weight of the polymer is 1.5-2.5 ten thousand, the molecular weight distribution is 1.7-1.9, and the thermal decomposition temperature of the polymer is more than or equal to 300 ℃.
The invention has the beneficial effects that: (1) compared with the existing solution method for preparing the polymer, the method adopts the ionic liquid as the solvent, so that the operation is more environment-friendly, and the polymer is safer to use; (2) the reaction temperature range is wide, and the reaction is stable and controllable; (3) the polymer obtained by the invention is a brand-new material, has good processing characteristics and thermal stability, and can be used as a rubber and plastic modifier or an additive.
Drawings
FIG. 1 is the thermogravimetric curve of the product of example 2.
Detailed Description
The present invention is further described below with reference to examples. It should be noted that the following examples are not intended to limit the scope of the present invention, and any modifications made on the basis of the present invention do not depart from the spirit of the present invention.
The required medicines are all commercial industrial products;
and measuring the molecular weight and the molecular weight distribution of the polymer by adopting Gel Permeation Chromatography (GPC), measuring a thermogravimetric loss curve by adopting a thermogravimetric analyzer, and reading out the thermal decomposition temperature of the polymer from the curve graph.
Example 1
(1) Under normal pressure, the glove box is replaced by nitrogen for three times, 3g of 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt and 10g of o-methylstyrene are added into a reactor in a low-temperature bath at the temperature of-10 ℃, and the mixture is stirred uniformly; (2) preparing an initiator in another mouth bottle in the low-temperature bath tank in the step (1): adding 0.2g of ethyl aluminum sesquichloride by using an injector, diluting with 2ml of hexane, shaking up and standing for 10 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 2 hours, adding 0.5g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate was 85%, the molecular weight of the polymer was 1.8 ten thousand, the molecular weight distribution was 1.7, and the thermal decomposition temperature of the polymer was 350 ℃.
Comparative example 1
The solvent adopts methane chloride to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion was 75%, the molecular weight of the polymer was 1.5 ten thousand, the molecular weight distribution was 2.6, and the thermal decomposition temperature of the polymer was 280 ℃.
Example 2
(1) Under normal pressure, the glove box is replaced by nitrogen for three times, 5g of 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt is added into a reactor in a low-temperature bath at the temperature of minus 50 ℃, 20g of m-methylstyrene is added, and the mixture is shaken up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 1g of ethyl aluminum sesquichloride by using an injector, shaking up, standing for 20min, and diluting with 5ml of hexane; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 4 hours, adding 0.5g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 87 percent, the molecular weight of the polymer is 2.0 ten thousand, the molecular weight distribution is 1.9, and the thermal decomposition temperature of the polymer is 410 ℃.
Comparative example 2
The solvent adopts methane chloride to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 73 percent, the molecular weight of the polymer is 1.6 ten thousand, the molecular weight distribution is 2.5, and the thermal decomposition temperature of the polymer is 290 ℃.
Example 3
(1) Under normal pressure, the glove box is replaced by nitrogen for three times, 5g of 1-octyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt is added into a reactor in a low-temperature bath at the temperature of-100 ℃, 10g of p-methylstyrene is added, and the mixture is shaken up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 1g ethyl sesqui aluminum chloride by using an injector, diluting with 1ml hexane, shaking up and standing for 10 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 1 hour, adding 2g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 84%, the molecular weight of the polymer is 2.5 ten thousand, the molecular weight distribution is 1.7, and the thermal decomposition temperature of the polymer is 360 ℃.
Comparative example 3
The solvent adopts methane chloride to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 76%, the molecular weight of the polymer is 1.8 ten thousand, the molecular weight distribution is 3.2, and the thermal decomposition temperature of the polymer is 270 ℃.
Example 4
(1) Under normal pressure, the glove box is replaced by nitrogen for three times, 3g of 1-octyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt is added into a reactor in a low-temperature bath at the temperature of minus 20 ℃, 15g of o-methylstyrene is added, and the mixture is shaken up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 1g ethyl sesqui aluminum chloride with an injector, diluting with 5ml hexane, shaking up and standing for 20 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 1 hour, adding 1g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 94%, the molecular weight of the polymer is 1.5 ten thousand, the molecular weight distribution is 1.9, and the thermal decomposition temperature of the polymer is 370 ℃.
Comparative example 4
The solvent adopts methane chloride to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 80%, the molecular weight of the polymer is 1.2 ten thousand, the molecular weight distribution is 2.0, and the thermal decomposition temperature of the polymer is 260 ℃.
Example 5
(1) Under normal pressure, the glove box is replaced by nitrogen for three times, 4g of 1-hexyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt is added into a reactor in a low-temperature bath at the temperature of minus 30 ℃, 10g of m-methylstyrene is added, and the mixture is shaken up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 1g ethyl sesqui aluminum chloride with an injector, diluting with 4ml hexane, shaking up and standing for 20 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 2 hours, adding 1.5g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 91 percent, the molecular weight of the polymer is 1.8 ten thousand, the molecular weight distribution is 1.9, the molecular weight distribution is 1.7-1.9, and the thermal decomposition temperature of the polymer is 310 ℃.
Comparative example 5
The solvent adopts dichloromethane to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 79 percent, the molecular weight of the polymer is 1.5 ten thousand, the molecular weight distribution is 2.6, and the thermal decomposition temperature of the polymer is 285 ℃.
Example 6
(1) Under normal pressure, the glove box is replaced by nitrogen for three times, 2g of 1-hexyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt is added into a reactor in a low-temperature bath at the temperature of-60 ℃, 20g of p-methylstyrene is added, and the mixture is shaken up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 1g ethyl sesqui aluminum chloride with an injector, diluting with 2ml hexane, shaking up and standing for 15 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 2 hours, adding 1g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 86%, the molecular weight of the polymer is 2.3 ten thousand, the molecular weight distribution is 1.8, and the thermal decomposition temperature of the polymer is 360 ℃.
Comparative example 6
The solvent adopts dichloromethane to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 78 percent, the molecular weight of the polymer is 1.8 ten thousand, the molecular weight distribution is 2.5, and the thermal decomposition temperature of the polymer is 280 ℃.
Example 7
(1) Under normal pressure, replacing nitrogen in a glove box for three times, adding a mixture (mass ratio is 1:1) of 5g of 1-octyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt and 1-hexyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt into a reactor in a low-temperature bath at the temperature of-80 ℃, adding 20g of o-methylstyrene, and shaking up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 0.2g of ethyl aluminum sesquichloride by using an injector, diluting with 5ml of hexane, shaking up and standing for 5 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 4 hours, adding 2g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 87 percent, the molecular weight of the polymer is 2.5 ten thousand, the molecular weight distribution is 1.7, and the thermal decomposition temperature of the polymer is 370 ℃.
Comparative example 7
The solvent adopts methane chloride to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 81 percent, the molecular weight of the polymer is 1.8 ten thousand, the molecular weight distribution is 3.0, and the thermal decomposition temperature of the polymer is 290 ℃.
Example 8
(1) Under normal pressure, replacing nitrogen in a glove box for three times, adding a mixture of 2g of 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt and 1-hexyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt (mass ratio is 1:1) into a reactor in a low-temperature bath at the temperature of-70 ℃, adding 20g of m-methylstyrene, and shaking up; (2) preparing an initiator in another bottle with a branch mouth in the low-temperature bath tank in the step (1): adding 1g ethyl sesqui aluminum chloride with an injector, diluting with 1ml hexane, shaking up and standing for 20 min; (3) and (3) adding the initiator prepared in the step (2) into a reactor, shaking up for reaction for 1 hour, adding 0.5g of methanol to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer. Measured according to the detection standard: the polymerization conversion rate is 84 percent, the molecular weight of the polymer is 2.2 ten thousand, the molecular weight distribution is 1.8, and the thermal decomposition temperature of the polymer is 350 ℃.
Comparative example 8
The solvent adopts methane chloride to replace ionic liquid, and the detection is carried out according to the detection standard: the polymerization conversion rate is 75%, the molecular weight of the polymer is 2.0 ten thousand, the molecular weight distribution is 3.5, and the thermal decomposition temperature of the polymer is 270 ℃.
The present invention is capable of other embodiments, and various changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (9)
1. A method for preparing an alkylstyrene polymer, comprising the steps of: under normal pressure, replacing nitrogen in a glove box for three times, adding ionic liquid serving as a solvent into a reactor in a low-temperature bath tank at the temperature of-10 to-100 ℃, adding alkyl styrene, and uniformly stirring; adding an initiator, continuously stirring for reacting for 1-4 hours, adding a terminator to terminate the reaction, settling, pouring, taking out a gel sample, and drying in a vacuum oven to obtain the polymer; the ionic liquid is an imidazolium salt; the initiator is ethyl aluminum sesquichloride.
2. The method as claimed in claim 1, wherein the low temperature bath in the glove box is at a temperature of-20 ℃ to-50 ℃.
3. The method of claim 1, wherein the alkylstyrene is one of o-methylstyrene, m-methylstyrene, p-methylstyrene, o-ethylstyrene, m-ethylstyrene, p-ethylstyrene, o-propylstyrene, m-propylstyrene, p-propylstyrene or styrene having a side chain of C4-C10 in an amount of 10-20 g.
4. The process of claim 1 wherein said alkylstyrene is o-methylstyrene.
5. The method according to claim 1, wherein the ionic liquid is used in an amount of 2 to 5 g.
6. The method according to claim 1, wherein the ionic liquid is one of 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt, 1-octyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt), 1-hexyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide salt, or a mixture thereof.
7. The method according to claim 1, wherein the terminating agent is methanol in an amount of 0.5 to 2 g.
8. The method according to claim 1, wherein the amount of the initiator is 0.2 to 1 g.
9. The method of claim 1, wherein said initiator is formulated as follows: preparing an initiator in another bottle with a mouth in the glove box low-temperature bath tank, adding 0.2-1 g of ethyl aluminum sesquichloride by using an injector, diluting with 1-5 ml of hexane, shaking up and standing for 5-20 min.
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